Source Title:
Open Chemistry
|
Volume/Issue:
Volume 8: Issue 4

Spectroscopic, thermal and toxicity studies of some 2-amino — 3- cyano — 1, 5 -diphenylpyrrole containing Schiff bases copper (II) complexes

Hanaa El-Boraey 1 , Randa Abdel-Rahman 2 , Ensaf Atia 1 , and Khalid Hilmy 1
  • 1 Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Kom, 23511, Egypt
  • 2 Department of Pest Physiology, Plant Protection Research Institute, Agricultural Research Center, Dokki, 12611, Giza, Egypt
DOI:
https://doi.org/10.2478/s11532-010-0046-7
|
Published online:
17 Jun 2010
PDF

Abstract

Two novel Schiff base ligands of 2-amino-3-cyano-1,5-diphenylpyrrole and salicylaldehyde (HL1) or 2- hydroxy1-naphthylaldehyde (HL2) and their copper(II) complexes have been synthesized and characterized by elemental analyses, spectral (UV-Vis, IR, EPR, Mass (for ligands)), thermal (DTA-TGA) methods, magnetic and conductance measurements. IR results demonstrate the bidentate binding of the Schiff base ligands involving azomethine nitrogen, phenolic or naphtholic oxygen and suggest the presence of HL2 and complexes (1, 2, 4 and 8) in enolimine-ketonamine tautomeric forms in the solid state. The EPR spectral data of complexes (2, 5, 6) show that the metal — ligand bonds have considerable covalent character. The thermal studies show that complexes (1, 2, 4 and 8) that are present in enolimine-ketonamine tautomeric forms exhibit lower thermal stability. The effect of synthesized ligands (HL1, HL2) and complexes (1, 5) were tested on the mortality of entomopathogenic nematodes (EPN) (Heterorhabditis bacteriophora and Steinernema carpocapsae). The study shows that the mortality of the nematodes increased with increasing concentrations of copper(II) ion, ligands and complexes. Copper(II) ion was the most toxic for EPN.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • [1] V. Alexander, Chem. Rev. 95, 273 (1995) http://dx.doi.org/10.1021/cr00034a002

  • [2] D.E. Fenton, H. Okawa, Chem. Berl. 130, 433 (1997) http://dx.doi.org/10.1002/cber.19971300402

  • [3] S.R. Collinson, D.E. Fenton, Coord. Chem. Rev. 148, 19 (1996) http://dx.doi.org/10.1016/0010-8545(95)01156-0

  • [4] D.E. Fenton, Pure Appl. Chem. 58, 1437 (1986) http://dx.doi.org/10.1351/pac198658111437

  • [5] P.A. Vigato, S. Tamburini, L. Bertolo, Coord. Chem. Rev. 251, 1311 (2007) http://dx.doi.org/10.1016/j.ccr.2006.11.016

  • [6] Z.H. Chohan, S.K.A. Sheazi, Synth. React. Inorg. Met-Org.Chem. 29, 105 (1999)

  • [7] C. Jayabalakrishnan, K. Natarajan, Synt. React. Inorg. Met-Org.Chem. 31, 983 (2001) http://dx.doi.org/10.1081/SIM-100105255

  • [8] T. Jeeworth, H.L.K. Wah, M.G. Bhowon, D. Ghoorhoo, K. Babooram, Synt. React. Inorg. Met-Org. Chem. 30, 1023 (2000)

  • [9] N. Dharmaraj, P. Viswanalhamurthi, K. Natarajan, Transition Met. Chem. 26,105 (2001) http://dx.doi.org/10.1023/A:1007132408648

  • [10] C.H. Colins, P.M. Lyne, Microhiul Methods (University Park Press, Baltimore, 1970) 422

  • [11] K.S. Abou-Melha, Spectrochim. Acta A 70, 162 (2008) http://dx.doi.org/10.1016/j.saa.2007.07.023

  • [12] T. Rosu, A. Gulea, A. Nicolae, R. Georgescu, Molecules 12, 782 (2007) http://dx.doi.org/10.3390/12040782

  • [13] M.A. Neelakanta, F. Rusalraj, J. Dharmaraja, S. Johnsonraja, T. Jeyakumer, M.S. Pillai, Spectrochim. Acta A 71, 1599 (2008) http://dx.doi.org/10.1016/j.saa.2008.06.008

  • [14] N. Goswami, D.M. Eichhorn, Inorg. Chem. Acta 303, 271 (2000) http://dx.doi.org/10.1016/S0020-1693(00)00047-5

  • [15] C.D. Berdanier, J.L. Groff, S.S. Gropper, Advanced Nutrition and Human Metabolism, 3rd edition (Wordsworth/Thompson Learning, CA, Belmont, 1999)

  • [16] A.S. Brill, R.B. Martin, R.J.P. Williams, Electronic Aspects of Biochemistry (Academic Press Inc., New York, 1964)

  • [17] E. Frieden, S. Osaki, H. Kobayashi, J. Gen. Physiol. 49, 213 (1965) http://dx.doi.org/10.1085/jgp.49.1.213

  • [18] J.A. Halfen et al., Science 271, 1397 (1996) http://dx.doi.org/10.1126/science.271.5254.1397

  • [19] R.M.S. Pereira et al., Molecules 12, 1352 (2007) http://dx.doi.org/10.3390/12071352

  • [20] I.B. Afanasév, E.A. Ostrakhovitchm, E.V.M. Chik, G.A. Ibraginova, L.G. Korkina, Biochem. Pharmacol. 61, 67 (2001) http://dx.doi.org/10.1016/S0006-2952(00)00528-1

  • [21] S. Chandra, D. Jain, A.K. Sharmaa, Spectrochim. Acta A 71, 1712 (2009) http://dx.doi.org/10.1016/j.saa.2008.06.028

  • [22] A.M. Koppenher, E.M. Fuzy, Biolog. Control 48, 63 (2009)

  • [23] P.S. Grewal, R.-U. Ehlers, D.I. Shapiro-Ilan, Nematodes as Biocontrol Agents (CABI Publishing, Wallingford, UK, 2005) http://dx.doi.org/10.1079/9780851990170.0000

  • [24] H.K. Kaya et al., Biolog. Control 38, 134 (2006) http://dx.doi.org/10.1016/j.biocontrol.2005.11.004

  • [25] H.K. Kaya, R. Gaugler, H.K. Kaya (Eds), Soil ecology (CRC Press, Boca Raton, Florida, 1990) 93

  • [26] G.O. Poinar, J. Rev. Nematology 11, 359 (1988)

  • [27] N. Ishibashi, D.R. Choi, E. Kondo, J. Nematology 19 (1987)

  • [28] N. Ishibashi, S. Takii, J. Nematology 25, 204 (1993)

  • [29] A. Dumestre, S. Sauve, M. McBride, P. Baveye, J. Berthelin, Archives of Environmental Contamination and Toxicology 36, 124 (1999) http://dx.doi.org/10.1007/s002449900451

  • [30] K.M. Hilmy, E.B. Pedrsen, Liebigs Ann. Chem. 1145 (1989)

  • [31] P.W. Selwood, Magnetochemistry (Interscience Publisher Inc., New York, 1956)

  • [32] F.M. El-Assal, M.H. El-Bishry, R.M. Abd El-Rahman, Egypt. J. Biolog. Pest Control 12, 15 (2002)

  • [33] M. Jaworska, J. Sepiol, P. Tomasik, Water, air and soil pollution 88, 314 (1994)

  • [34] D.B. Duncan, Multiple ranges and multiple F-test. Biometrics 11, 1 (1955)

  • [35] W.J. Geary, Coord. Chem Rev. 7, 81 (1971) http://dx.doi.org/10.1016/S0010-8545(00)80009-0

  • [36] W.K. Dong, Y.X. Sun, Y.P. Zhang, L. Li, X.N. He, X.L. Tang, Inorg. Chim. Acta. 362, 117 (2009) http://dx.doi.org/10.1016/j.ica.2008.03.128

  • [37] G.B. Bagihalli, P.G.A.S. Patil, P.S. Badami, Med. Chem. 43, 2639 (2008)

  • [38] Z.H. Abd El.-Wahab, Spectrochim. Acta A 67, 25 (2007) http://dx.doi.org/10.1016/j.saa.2006.05.038

  • [39] S.A. Abdel-Latif, H.B. Hassib, Y.M. Issa, Spectrochim. Acta A, 67, 950 (2007) http://dx.doi.org/10.1016/j.saa.2006.09.013

  • [40] V.P. Daniel, B. Murukan, B.S. Kumari, K. Mohanan, Spectrochim. Acta A, 70, 403 (2008) http://dx.doi.org/10.1016/j.saa.2007.11.003

  • [41] M. Tumer, H. Koksal, M.K. Sener, S. Serin, Transition Met. Chem. 24, 414 (1999) http://dx.doi.org/10.1023/A:1006973823926

  • [42] A.M. Donia, H.A. El-Boraey, Transition Met. Chem. 18, 315 (1993) http://dx.doi.org/10.1007/BF00207955

  • [43] H. Temel, S. Ilhan, Spectrochim. Acta A 69, 896 (2008) http://dx.doi.org/10.1016/j.saa.2007.05.041

  • [44] N. Galic, Z. Cimerman, V. Tomisic, Spectrochim. Acta A 71, 1274 (2008) http://dx.doi.org/10.1016/j.saa.2008.03.029

  • [45] L. Antonov, W.M.F. Fabian, D. Nedeltcheva, F.S. Kamounah, J. Chem. Soc. Perkin Trans. 2, 1173 (2000)

  • [46] J.B. Lambert, H.F. Shurvell, L. Verbit, R.G. Cooks, G.H. Stout, Organic Structural Analysis (Macmillan, New York, 1976)

  • [47] F.A. EL-Saied, M.I. Ayad, R.M. Issa, S.A. Aly, Polish J. Chem. 75, 941 (2001)

  • [48] J.M. Ramos, R.M. Viana, C.A.S. Téllez, W.C. Pereira, A.O. Izolani, M.I.P. da Silva, Spectrochim. Acta A 65, 433 (2006) http://dx.doi.org/10.1016/j.saa.2005.09.047

  • [49] A.M. Donia, H.A. ElBoraey, J. Anal. Appl. Pyrolysis 63, 69 (2000) http://dx.doi.org/10.1016/S0165-2370(01)00142-5

  • [50] A.A.A. Emara, B.A. El-Sayed, E.A.E. Ahmed, Spectrochim. Acta A 69, 757 (2008) http://dx.doi.org/10.1016/j.saa.2007.05.028

  • [51] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th edition (John Wiley and Sons, New York, 1997)

  • [52] M.S. Nair, R.S. Joseyphus, Spectrochim. Acta A 70, 749 (2008) http://dx.doi.org/10.1016/j.saa.2007.09.006

  • [53] S.M. Abu-El-Wafa, A. Salibk, G. El-Manyand, T.M. Ismial, Synth. React. Inorg. Met-Org. Chem. 20, 1343 (1990) http://dx.doi.org/10.1080/00945719008048638

  • [54] A.B.P. Lever, Inorganic Electronic Spectroscopy, 2nd edition (Elsevier, New York, 1984)

  • [55] M.F. Iskander, M.A.E. Shaban, S.M. El-Badry, Carb. Res. 338, 2341 (2003) http://dx.doi.org/10.1016/S0008-6215(03)00379-3

  • [56] V.T. Getova, R.P. Bontchev, D.R. Mehandjiev, V. Skumryev, P.R. Bontchev, Polyhedron 24, 1983 (2005) http://dx.doi.org/10.1016/j.poly.2005.05.017

  • [57] A.B.P. Lever, Inorganic Electronic Spectroscopy (Elsevier, Amsterdam, 1986)

  • [58] S.K. Padhi, V. Manivannan, Polyhedron 26, 1619 (2007) http://dx.doi.org/10.1016/j.poly.2006.11.046

  • [59] P.B. Sreeja, M.R. Prathapachandra Kurup, A. Kishore, C. Jasmin, Polyhedron 23, 575 (2004) http://dx.doi.org/10.1016/j.poly.2003.11.005

  • [60] N.M. Shauib, A.A. Elassar, A. El-Dissouky, Spectrochim. Acta A 63, 714 (2006) http://dx.doi.org/10.1016/j.saa.2005.06.024

  • [61] R.N. Prasad, M. Mathur, J. Serb. Chem. Soc. 67, 825 (2002) http://dx.doi.org/10.2298/JSC0212825P

  • [62] F.K. Kneubuhl, J. Chem. Phys. 33, 1074 (1960) http://dx.doi.org/10.1063/1.1731336

  • [63] H.R. Garmen, J.D. Swallen, J. Chem. Phys. 56, 3221 (1962)

  • [64] P. Kamalakannan, D.V. Russ, J. Coord. Chem. 28, 423 (2002) http://dx.doi.org/10.1023/A:1016032928816

  • [65] A.T.A. Mubarak, A.Z. EL-Sonbati, A.A. EL-Bindary, Appl. Orgo. Metal Chem. 18, 212 (2004) http://dx.doi.org/10.1002/aoc.606

  • [66] B.N.B. Raj, M.R.P. Kurupa, E. Suresh, Spectrochim. Acta A 71, 1253 (2008) http://dx.doi.org/10.1016/j.saa.2008.03.025

  • [67] D. Kivelson, R. Neiman, J. Chem. Phys. 35, 149 (1961) http://dx.doi.org/10.1063/1.1731880

  • [68] S.N. Shetti, A.S.R. Murty, G.L. Tembe, J. Indian Chem. 32A, 318 (1993)

  • [69] H.A. El-Boraey, J. Therm. Anal. Cal. 81, 1 (2005) http://dx.doi.org/10.1007/s10973-005-0789-0

  • [70] H.A. El-Boraey, A.M. Donia, M.F. El-Samalehy, J. Anal. Appl. Pyroplysis 73, 204 (2005) http://dx.doi.org/10.1016/j.jaap.2004.10.001

  • [71] A.M. Donia, H.A. El-Boraey, M.F. El-Samalehy, J. Therm. Anal. Cal. 73, 987 (2003) http://dx.doi.org/10.1023/A:1025875707494

  • [72] H.A. El-Boraey, F.A. El-Saied, S.A. Aly, J. Therm. Anal. Cal. 96, 599 (2009) http://dx.doi.org/10.1007/s10973-008-9197-6

  • [73] J.P. Liao, X.G. Lin, Z.H. Cao, Y.Q. Shi, M.H. Wong, Chemosphere 50, 847 (2003) http://dx.doi.org/10.1016/S0045-6535(02)00229-1

  • [74] B. Helling, S.A. Reinecke, A.J. Reinecke, Extoxicolo and Enviro. Safty 46, 108 (2000) http://dx.doi.org/10.1006/eesa.1999.1880

OPEN ACCESS

Journal + Issues

Open Chemistry

Online ISSN:
2391-5420
First published:
01 Mar 2003
Language:
English
Publisher:
De Gruyter

Search